HCID 21906633, compound → HCID 21906165, compound

HRID 988656Notes

Reaction equation

HRID 988656 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH:17][C:18]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:19]=2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)=[O:21])=[O:16])[CH2:11][CH2:10]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH:17][C:18]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:19]=2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)=[O:21])=[O:16])[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 21906633HCID 21906633, compound

Product 1

HCID 21906165HCID 21906165, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-[[4-(tert-Butoxycarbonylamino)cyclohexylcarbonyl]-amino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide (2.90 g, 5.71 mmol) was dissolved in TFA (10 mL). After 5 minutes, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride and methanol. The organics were washed with saturated aqueous sodium carbonate (2×50 mL) and water (50 mL). The organic layer was dried over sodium sulfate, filtered and concetrated to give the title product (1.86 g, 4.56 mmol, 80%) as a white solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionThe residue was diluted with methylene chloride and methanol
  3. washThe organics were washed with saturated aqueous sodium carbonate (2×50 mL) and water (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-65229771179442d5a14217e7761666f5
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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